


31 Days of Porn, Uglywettie Style - Day #7

by UglyWettieWrites



Series: 31 Days of Porn, Uglywettie Style [1]
Category: Brendan Block - Fandom, Secret Smile (TV)
Genre: 31 Days of Porn Challenge 2017, Anal Sex, Brendan Block - Freeform, Brendan meets his match, David Tennant - Freeform, F/M, Fanfic, Fanfiction, Femdom, Hardcore Erotica, Pegging, Secret Smile - Freeform, Squirting
Language: English
Status: Completed
Published: 2017-05-08
Updated: 2017-05-08
Packaged: 2018-10-29 11:12:34
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,232
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10852794
Author URL: https://archiveofourown.org/users/UglyWettieWrites/pseuds/UglyWettieWrites
Summary: Brendan Block meets a rich, beautiful woman at a bar and goes for it, ever confident he can get what he wants from her if she gives him the time of day...But she's a bit more complicated that he imagined.





	31 Days of Porn, Uglywettie Style - Day #7

He sidled up next to her in the bar, his face a vision.

Still, she looked into her martini. Her jaw tightened.

“Hello. I’m Brendan. I couldn’t help but notice-”

She cut him off. “I’m not your type, Brendan. Move along.” She took a sip of her dirty, dirty martini and used her tongue to pluck an olive from the cocktail stick, looking him right in the eye.

Lord, he was a beautiful bastard. But he would be, to do what he thinks he’s doing with her.

His smile didn’t move, but his eyes flashed anger. It only stoked her flame.

“It seems you’re the type of that blonde I saw you kissing goodbye, not 20 minutes ago.”

“She’s my sister,” he lied smoothly.

“You have an interesting relationship then,” she said, draining her glass. She nodded her head at the bartender, and he started making another one as a group of sorority girls on the other end of the bar waited. “Her hand was on your ass.”

“You were watching,” he said, leaning in closer. It was incredibly bold. She gave him an irritated look, but her mouth watered at the intense amber of his eyes. The bartender put the fresh drink in front of her, and she drank down half of it in one sip.

He was a wolf among rabbits. But she was always looking for a challenge.

“Do you like what you see?” he asked, his eyes moving down her body. She was still in her work clothes - three piece suit and heels. Her skin got hot wherever his eyes lingered.

“Your fiancee like you chatting up other women after she buys you dinner and drinks?”

He seemed to lose his composure for a second, then the walls came up again. She was far more clever than his usual prey. Ordinarily, he would walk away, but his appetite was already whetted. He liked the back and forth, and furthermore, he knew if he could get his teeth in her, she’d be a pussycat in his hands.

He had sweet dick, and he knew it.

“You have a problem with 50/50 give and take relationships?”

She chuckled. “I’m wealthy. I don’t need anyone else’s fifty percent. Also, I can smell a con man 100 yards off. It’s kinda my job to know.”

His eyebrow rose, but again, his face remained set.

“What do you do?”

She turned to him, and his eyes lingered on her legs. She waited patiently for him to look her in the eye.

“None of your goddamned business, Brendan.”

Again, his resolve seemed to flag, but to her delight, he rallied. “Fair enough. Maybe you’re a spy.”

“Sure, slugger,” she said, draining her second drink. She was feeling fine as wine, and ready for some fun. “Is she expecting you anytime soon?”

He took a deep breath, and shook his head. “I come home when I want. She’s not my mum.”

She slid off the barstool and cocked her head at the bartender. He pulled her bag from underneath the bar and handed it to her.

“Thanks, gorgeous. You’re doing a brilliant job. The place is hopping,” she said. The bartender, who was in fact the general manager of the restaurant, glowed at her compliment. After all, she owned the place, and many like it.

“Thank you, madame,” he said, and then turned to take care of a customer.

She went into her bag for her cell and took her time. He stood still beside her, waiting for her to speak. After typing a couple of text messages, she started walking toward the door. Halfway, she turned to see he still stood at the bar, staring.

She slapped her thigh, once, and cocked her head, beckoning. He followed.

He had to run the last bit, since the valet already had her car waiting, and she was stepping into it. It was an impossibly expensive looking Mercedes with a drop top and chrome wheels. It was a shimmery darkest blue. Envy prickled at him, but he swallowed it down.

One go, and she’d be handing him the keys.

He got into the passenger’s seat and she stepped on the gas, making the wheels squeal as she slid smoothly into traffic. Her jacket was open, revealing a silk blouse and a vest cut right underneath her plentiful breasts. The blouse was open down to the vest, and the scalloped edge of her bra was clearly visible. Her skirt rode up her thighs as she popped the clutch artfully, and her eyes remained on the road despite his intense stare.

The smallest smile played on her lips.

They stopped at a red light. “My place is not too far from here, but I’m horny. You want to touch me?” she said bluntly.

He put his hand on her knee and slid it up the inside of her thigh until it disappeared underneath her skirt. He sighed as his fingers touched silky, hot flesh. No panties. He caressed her gently, parting her lips to find her clit.

She spread her legs and pressed his hand into her. “Don’t get shy now, boy. I’m not in the mood for teasing.”

He shrugged and slid three fingers into her, making her groan. He pumped quick and hard, rubbing her clit with the flat of his palm. Her scent filled the cabin, and his cock throbbed in his pants. Her thighs moved liquidly against his wrist as she shifted gears, but her eyes were nearly closed with passion.

She turned abruptly into the parking garage of a high rise apartment building. The door slid open slowly, and she ground into his hand, even as a guard stared at them from the little booth just 6 feet away.

“Don’t stop,” she said when he hesitated. She pulled her skirt up, keeping eye contact with the pudgy pale man. He dropped his sandwich and flushed scarlet.

His heart beat in his ears. It was exhilarating. The doors finally clicked all the way open and she drove past. Her squealing wheels echoed in the small garage, and she pulled into a parking spot with a personalized sign.

He moved to open the door, and she slapped him.

“ _Don’t stop_.”

He didn’t rub his stinging face, leaning into her to finger her deep as he could. She flooded around his fingers and put her leg up to give him better access. A couple drove past and parked nearby. She pulled him to her lap and pressed his face to her pussy. He licked eagerly, sucking her clit.

She held off her orgasm until the couple was just feet away. She cried out and slapped the foggy glass, grinding her pussy into his mouth. The couple remained poker-faced as they stepped into the elevator.

He sat up, wiping his face. She pulled her skirt down and got out of the car without a word. Again, he followed her into an elevator. She flashed a card in front of a reader and they started to move. She stared at him with hungry eyes. Her handprint was still on his face. She rubbed his cock through his pants. He leaned against the wall and closed his eyes.

When the door opened, she pulled him gently by his bulge into her apartment. It was huge. They were in a marble foyer with an art deco chandelier and a table with an arrangement of fresh peonies. Two curling staircases met in the second floor.

The city sparkled in the living room beyond the staircases.

Fuck, he thought. She wasn’t lying. She wasn’t just rich. She was wealthy. 

She squeezed him, bringing his attention back to her.

“Come with me,” she said, climbing the stairs. He caressed her legs, kissing the backs of her thighs. She ran and opened the double doors into her bedroom. Her bed was in the middle, a solid cast iron canopy frame festooned with sheer silk that rippled with the slightest breeze coming in from the open doors to the terrace.

She closed the bedroom doors and leaned on them.“Take off your clothes, Brendan. Every stitch.”

She watched him as he unbuttoned his shirt, pulling it off slowly and throwing it on the floor. His nipples hardened in the breeze. He unbuckled his belt, stepped out of his jeans, then kicked off his shoes.

He was slim but luscious, exactly her type, since the wiry were resilient. They could take a lot.

He pulled off his socks and walked toward her, his half hard cock bouncing. She held up her hand.

“Do you usually get in cars with strange women? You haven’t even asked my name.”

“I don’t care about your name,” he said.

She laughed. “I like a frank man in my bedroom. Makes for a better fuck.”

He took a step forward, stroking himself harder for her. He pushed her gently against the door, pressing his cock against her hip, and moving her hand there. She sighed, but when he went in for a kiss, she shook her head.

“A man’s got to earn my kisses,” she said, putting her finger on his lips.

He gave her a long look, then shrugged. Her hand squeezed his cock, but did not move.

“I want to fuck you,” she said, running her fingers through his thick hair. He kissed her neck, his hand going underneath her skirt again. She squeezed it between her thighs. “Did you hear me?”

“Come to bed, then,” he said.

She shook her head again, biting her lip as she stared at his body.

“I want to _fuck_ you,” she said. Her hand moved down his back, to his ass and between his cheeks. She pressed the tip of her index finger in his asshole. He gasped, then took a step back.

“I don’t...do that,” he said.

She was impassive. “Then there’s the door,” she said, kicking the door behind her. He picked up his pants from the floor and began to put them on. “But, just to let you know, I am very, very generous to the boys who allow me my one little pleasure.”

He picked up his shirt. She walked to a bureau near her bed and pulled out a lacquered box. Inside, there was a strap-on. The dildo looked realistic, and cast in a silicone identical to her skin color. He couldn’t help staring at it. It was larger than he was, and he wasn’t small. He was so distracted with the toy he didn’t see the wad until she threw it on the bed beside the toy.

Hundred pound notes. And the wad was thick as his cock.

“You’re free to go. But if you stay, there’s a lot more where that came from.”

He swallowed hard. The situation had gone out of his control. “I’m not a hooker.”

She sniffed. “You’re working mighty hard for your fiancee’s money.” She disappeared into her closet. He was tempted to bolt, but that wad of cash on the bed could finance his freedom from the silly bitch he was conning now. His instincts were telling him to run, but was sick of giving himself away for chips. He wanted a gleaming apartment in the sky. He wanted to entice pretty women into his car and tell them to blow him.

Tell, not ask, knowing they would for a taste of the good life. It was what he was meant to be, but he had not met someone who could take him there.

She walked back into the bedroom, nude except for stockings, garter belt, and a shiny pair of black latex gloves. Her face was clean - she had wiped away her eyeshadow and lipstick. For some reason, it accentuated her features. She was beautiful, and she knew it. They were the same kind, so she already knew he wouldn’t go.

He sat on the bed, eyeing the dildo. She walked between his legs and caressed his body, kissing his neck.

He started to lay back, but she clicked her tongue. “Oh no. You’ve got to freshen up first. I know it will take a bit, but you’re worth the wait. I’ll be here when you come out.” She pointed to the bathroom door. “There’s a closet in there. Inside is the equipment, and the directions.”

She climbed into bed, moving her hips enticingly. He licked his lips.

He walked into the bathroom and just like she said, there was a narrow closet by the door. Inside, there was a basket of plastic-wrapped bulb syringes. Beside them, there were bottles of saline. There was a cards with directions in both packages.

_Fill syringe with saline, 90%_

_Lube anus. Sit on toilet._

 

_Insert syringe into rectum…_

A giggle bubbled out of his mouth.

Of course. A pre-anal ritual.

If anything, he wished some of the women he’d fucked thought of it. But this woman was a professional. It was daunting.

He couldn’t use his everyday game with her. He would have to take it the furthest he ever has to earn her trust. He looked around at the white marble and the art deco fixtures. Bottles of perfume you couldn’t find in Harrod’s sat on her bathroom vanity, shining like topaz in the soft lighting. He wanted it.

She wanted in? He would give her a show she wouldn’t soon forget. He ripped open the plastic packaging and got to work.

* * *

 He walked out, naked and sparkling.

She was riffling through a lifestyle magazine on her bed, still gloved and loose limbed with anticipation.

“Come here,” she said, patting the bed beside her. He sat and looked. It was a five page spread of a hotel in the south of France. It was indescribably beautiful. He wanted to lay in the white sand under the palm trees, ogling the frenchwomen as they walked by.

“It’s mine. I opened it just six months ago. It’s already damn near paid itself off,” she said, winking. She traced down his chest to his cock. “Lay on the bed, face down.” He moved slowly. She slapped his ass. “Get moving.” 

“Let’s see how well you did,” she said, spreading his legs and kneeling between them. She caressed up his thighs, then squeezed his bum. “Mmm, you’re tight.” He jumped as she bit him. She spread him open, and he felt the heat of her breath on his winking hole. “You are a good, good boy,” she purred, and licked him.

His toes curled as she gently cupped his balls. Her tongue danced around his puckered flesh and poked into him. He arched, raising his hips off the bed.

“You’re a natural,” she said, and stroked him to life as her tongue muscled deeper and deeper into his ass. He sighed, his hands turning to fists on her sheets. It wasn’t so bad. In fact, it was very good.

Her tongue swirled down past his perineum to his balls, sucking each one into her mouth, never stopping her stroking. He raised his ass higher in the air. She licked down his shaft, then lay on her back with her upturned face between his legs. He bucked forward, pushing past her lips. She moaned as he slowly pumped himself in and out of her mouth, sucking noisily, her tongue flicking over his frenulum. He was so distracted with her eager sucking he didn’t feel her hands moving up his thighs again.

She slid her middle finger into his ass. There was no resistance due to the slippery latex, but he ached. His heartbeat increased. His stomach muscles tightened.

She licked her spittle off his cock. “You can’t tense up, beautiful. It will hurt more.” She jerked him, stroking his foreskin with her thumb, then sucking it as her tongue danced just inside of it, licking the head of his cock. He groaned and relaxed. She slid another finger inside him.

He trembled. Her fingers felt lubed, but it hurt. Sweat made the pillowcase damp. She worked her two fingers inside him far past the second knuckle in the same rhythm as she sucked him.

Despite the pain, his cock throbbed. She slurped his precum and moaned. “Relax. The goal isn’t pain, it’s pleasure.” She curled her fingers and suddenly he felt a pressure that took his breath away. He cried out, curling into himself. She chuckled.

“Isn’t that yummy?” she said, massaging just inside the tight ring of muscle. He arched like a cat and nodded. The pain was still there, but it just wasn’t important anymore. She started to rub her thumb on his lubeslick perineum as she massaged, and he let out a long groan. Never in all his days had he felt something like that. It was...beyond orgasm good, yet he had not come yet.

She worked a third finger into him. Again he ached, and sweat, but her rhythm was steady and delicious.

“I want you,” she said, and stopped abruptly. He whimpered, and surprisingly, felt empty as she withdrew her fingers.

She put on the strap-on and rolled a condom onto it as he stared. It was big, and thick, and veined like a real cock. He flushed, suddenly unsure. She kissed his neck, softly, nipping him and teasing a moan out of him.

“Don’t be scared," she said in his ear. “I can guarantee you’ll like it as much as I do by the end.” Her mouth moved down his body. She licked each of his nipples, then buried her nose in the silky hair between his legs. “So good.”

She grabbed a pillow and put it underneath his ass. “Knees up, honey.” He obeyed. He felt exposed. His cheeks reddened. She licked from underneath his cock to his asshole again. This time, she was able to get it in, and her prehensile teasing made him gasp.

“I could spend an hour down here,” she said, licking lube off her lips.

She squeezed more lube generously on him, and gently worked it inside him with her gloved fingers. “That’s good. _Relax_ ,” she said, bending to nip at his thighs.

She lubed the dildo, stroking his half hard cock in the same rhythm. It was hypnotizing. She climbed on top of him, rubbing her body against his. The dildo slid easily in the crack of his ass, but she teased, kissing down the line of his jaw. Her breasts were a delicious pressure on his chest, and he squeezed them, tugging at her nipples. His cock slid against her belly, and he hardened fully again. He was enjoying the friction when he felt the tip pressing against his hole. She became very still and cradled his neck. It started to open him up, centimeter by centimeter. Her body was tense above him, and her breath was getting heavy.

Could she feel his tightness and heat? It’s as if she could.

“Breathe, honey,” she said. She licked his ear. It moved deeper inside of him, aching until the crown finally popped past his ring of muscle. He arched and groaned, but his body received the rest of it with scary ease. She was in him.

“How does it feel?” she asked, her mouth hot on his neck.

The stretch ached, but it was not excruciating like so many women professed it was. It was...a breathless feeling. He panted. His muscles tried to squeeze her out, but she rolled her hips forward, slowly, and worked herself in a bit deeper. Her lips were pressed on his neck.  His thighs pressed against her hips. She rolled her hips again, moaning into his skin. He echoed her moan. His hands moved down her arms, to her hips.

“Tell me,” she said, her breath short.

He rolled his hips into her, pulling her deeper into him. She looked into his eyes as she began to fuck him faster. He spread wider and bit his lip. His eyes were golden, welcoming.

“Naughty wolf,” she said, and grabbed his shoulder for leverage. Her other hand was flat on his chest, and she worked herself in and out so she massaged his prostate with every stroke.

He panted harder. She stared at him, drunk on his gaze alone.

“Do you like it?” she asked. Her long hair tickled his shoulders. She licked his bottom lip.

She was almost where he wanted her.

“I want to try it from the back,” he said.

She withdrew. Again, he felt empty.

He turned quickly and offered himself. This time, she slid inside with ease. He turned to look at her, licking his lip where she licked. She groaned and fucked into him, her fingers digging into his slim hips.

The sensation, it was different this way. Deeper. Maybe it was the position but he was panting again, and not pretending his pleasure. He put his forehead against the cool iron of her headboard. He was hard, and she reached around to stroke him. Her thighs were pressed against the backs of his, and he could smell her arousal again.

He parried every thrust better than any man she’d had in years. His freckled back, rippled with muscle, was slick with sweat and his face crumpled with pleasure. He was exquisite. The dildo sucked her clit with every thrust, but she was aching to be fucked. She made up her mind. She would take him with her, and know more about his delicious body and his degenerate mind.

She withdrew. The beautiful beast actually whimpered as she unbuckled the strap on and took it off. She pulled off her gloves and threw them.

“Turn around,” she said, and pawed in her tangle of sheets for a fresh condom. She rolled it on his cock then got on her hands and knees in front of him. He could see the red where the leather rubbed on her hips and thighs. Her pussy was sloppy wet, and swollen with arousal. “My turn,” she said. He sank into her. 

She was tight as new flesh. He fucked her hard, feeling it’s what she needed from him. She was wanton, turning to look at him as he had her, encouraging him.

He stilled his hips and she popped her pussy on him, stroking him off. He let her take him, ghosting his fingers on her jiggling ass. His thumb caressed her slick asshole.

“Put it in,” she said. He wet his fingers in her copious pussy juice and obeyed. She was elastic and hot. His eyes narrowed. She saw. “Do it.” She threw the bottle of lube to him and he dripped it down her crack, rubbing it in. “Now.”

He pushed his way in her ass and her heat made him tingle. She put her face in the pillows. He felt her energy spike. She loved it.

“Don’t be gentle,” she said through gritted teeth. Her brow was furrowed. He had her.

He grabbed her hips and pounded into her. She opened up quickly and groaned into the pillow with each thrust, grabbing fistfuls of sheet. He reached around to stroke her clit, but she bucked his hand away.

“Fuck me,” she said, her eyes getting the avid look of the hungry. “Deep.”

He was in her all the way to the root. Her moans turned to cries that made him desperate. He caressed the insides of her wet thighs. The heat of her cunt radiated to his fingers. She dripped pointlessly to the sheets, and he wanted to drink her down. He touched her with his thumb greedily, wishing he could fill her both places at once.

She suddenly sat up, pressing her body against him. She reached behind to run her fingers through his hair. 

“Keep doing...that,” she said, talking about fingering her as he fucked her ass. “Faster.” She pulled his hair. 

She groaned and grabbed the headboard.“Harder!” she said. “ _Harder harder harder_ …” Her muscles snapped around him, and she wet his hand to the wrist as she squirted. He put three fingers inside her to feel it, and she rocked into him. Her sucking on his fingers and his cock with her muscles triggered his own orgasm. She finally pulled his face to hers for a kiss. He smiled and slid his tongue in her mouth and let her suck it.

He withdrew and lay back, holding his arms out to her. She stared for a couple of seconds, then crawled into his arms, softly licking the sweat from his chest.

“Brendan,” she said, looking him in the eye. “I have to go to France in the morning. Come with me.”

He sat up, faking indignation. “But, what about my fiancee?”

She rolled her eyes. “Don’t pretend you care to me, little wolf. Come.”

“Little wolf?” he said.

“Little now. But means could make you truly dangerous,” she said, winking at him and giggling.

He looked at her, mystified. He’d never met a woman he couldn’t best. He thought he had bested her, but how, since she saw his true nature? Again, he felt not completely in control.

She reached between his legs to pinch the condom from his cock, then sucked her fingers clean.

“Warm turquoise waters, easily impressionable young men and women, and a 150 foot yacht that can reach international waters in hours.”

Her intense gaze gave him goosebumps.

“Yes,” he said. “Absolutely.”

 

And so, he sank quietly, without a fight, into the void.


End file.
